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Bile acid


DATA No : BBA0058 INFORMANT : Takashi Iida

NAME : 1b,3a,7a-Trihydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:266-270degC, (Me ester-7-acetate; mp, 93-95degC)(Ref. 0016)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-22: +4.3deg (C=0.268, MeOH) (Me ester-7-acetate)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 3380, 3280, 1705(Ref. 0016)

NMR SPECTRA:1H-NMR (Pyridine-d5; 90MHz) d: 18-Me 0.69(s), 19-Me 1.30(s), 7b- H 3.92-4.10(m), and 1a-H 4.12-4.28(m), 3b-H 4.40-4.78(m)(Ref. 0016)

MASS SPECTRA:Me-TMS ether (70eV) m/z: 623(M-15), 548(M-TMSOH, 3%), 458(M-2TMSOH, 9%), 368(M-3TMSOH, 16%), 217 (100%)(Ref. 0016)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from human urine.(Ref. 0001)
Detected in human meconium.(Ref. 0016/0186)
Primary bile acid in pheasant and pigeon.(Ref. 0102)
Biliary bile acid of fruit pigeons and doves (Columbiformes).(Ref. 0102/0103/0166)
Fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Excreted in urine of healthy newborn.(Ref. 0194/0210)
Isolated from human fetal gallbladder bile.(Ref. 0198)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Identified in urine, bile, portal and peripheral venous sera, and liver tissues from subjects with liver diseases (cholestasis, liver cirrhosis, chronic hepatitis, acute hepatitis).(Ref. 0200/0201)
Identified in urine of newborns.(Ref. 0245)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Hill, R. A., Kirk, D. N., Makin, H. L. J., and Murphy, G. M. (1991) Chemical Data, Structures and Bibliographies, in Dictionary of Steroids, Chapman & Hall, London.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0016]
AUTHOR:Tohma, M., Mahara, R., Takeshita, H., Kurosawa, T., and Ikegawa, S.
TITLE:Synthesis of the 1 beta-hydroxylated bile acids, unusual bile acids in human biological fluids PubMed ID:3769090
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:34 PAGE : 2890-2899 (1986)
[TOP]

[0102]
AUTHOR:Hofmann, A. F., Schteingart, C. D., and Hagey, L. R. (1995) Species Differences in Bile Acid Metabolism, in Bile Acids in Liver Diseases (Paumgartner, G., and Beuers, U. eds), pp 3-30, Kluwer Academic Publishers, Dordrecht.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0103]
AUTHOR:Hagey, L. R., Schteingart, C. D., and Hofmann, A. F. (1995) New, Natural Bile Acids: Implications for Bile Acid Evolution, in Bile Acids in Gastroenterology Basic and Clinical Advances (Hofmann, A. F., Paumgartner, G., and Stiehl, A. eds), pp 3-7, Kluwer Academic Publishers, Dordrecht.
TITLE:(Hagey, L. R. (1992), Ph. D. Thesis, Bile Acid Biodiversity in Vertebrates: Chemistry and Evolationury Implications, Universty of California. San Diego)
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0166]
AUTHOR:Hagey, L. R., Schteingart, C. D., Ton-Nu, H. T., and Hofmann, A. F.
TITLE:Biliary bile acids of fruit pigeons and doves (Columbiformes): presence of 1-beta-hydroxychenodeoxycholic acid and conjugation with glycine as well as taurine PubMed ID:7868982
JOURNAL:J Lipid Res.
VOL:35 PAGE : 2041-2048 (1994)
[TOP]

[0186]
AUTHOR:Mahara, R., Takeshita, H., Kurosawa, T., Ikegawa, S., and Tohma, M.
TITLE:Detemination of 1b-Hydroxylated Bile Acids and Related Compounds in Human Biological Fluids by Gas Chromatography-Mass Spectrometry.
JOURNAL:Anal. Sci.
VOL:3 PAGE : 449 -459 (1987)
[TOP]

[0190]
AUTHOR:Murai, T., Mahara, R., Kurosawa, T., Kimura, A., and Tohma, M.
TITLE:Determination of fetal bile acids in biological fluids from neonates by gas chromatography-negative ion chemical ionization mass spectrometry PubMed ID:9140754
JOURNAL:J Chromatogr B Biomed Sci Appl.
VOL:691 PAGE : 13-22 (1997)
[TOP]

[0194]
AUTHOR:Obinata, K., Nittono, H., Yabuta, K., Mahara, R., and Tohma, M.
TITLE:1 beta-hydroxylated bile acids in the urine of healthy neonates PubMed ID:1403443
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:15 PAGE : 1-5 (1992)
[TOP]

[0198]
AUTHOR:Setchell, K. D., Dumaswala, R., Colombo, C., and Ronchi, M.
TITLE:Hepatic bile acid metabolism during early development revealed from the analysis of human fetal gallbladder bile PubMed ID:3182806
JOURNAL:J Biol Chem.
VOL:263 PAGE : 16637-16644 (1988)
[TOP]

[0199]
AUTHOR:Shoda, J., Mahara, R., Osuga, T., Tohma, M., Ohnishi, S., Miyazaki, H., Tanaka, N., and Matsuzaki, Y.
TITLE:Similarity of unusual bile acids in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases PubMed ID:3411245
JOURNAL:J Lipid Res.
VOL:29 PAGE : 847-858 (1988)
[TOP]

[0200]
AUTHOR:Shoda, J., Osuga, T., Mahara, R., Tohma, M., Matsuura, K., Tanaka, N., Matsuzaki, Y., and Miyazaki, H.
TITLE:Altered metabolism of bile acids in cholestasis: determination of 1 beta- and 6 alpha-hydroxylated metabolites PubMed ID:2745625
JOURNAL:J Chromatogr.
VOL:488 PAGE : 315-328 (1989)
[TOP]

[0201]
AUTHOR:Shoda, J., Tanaka, N., Osuga, T., Matsuura, K., and Miyazaki, H.
TITLE:Altered bile acid metabolism in liver disease: concurrent occurrence of C-1 and C-6 hydroxylated bile acid metabolites and their preferential excretion into urine PubMed ID:2324645
JOURNAL:J Lipid Res.
VOL:31 PAGE : 249-259 (1990)
[TOP]

[0210]
AUTHOR:Wahlen, E., and Strandvik, B.
TITLE:Effects of different formula feeds on the developmental pattern of urinary bile acid excretion in infants PubMed ID:8126625
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:18 PAGE : 9-19 (1994)
[TOP]

[0245]
AUTHOR:Ikegawa, S., Yoshimura, T., Ito, K., Kurosawa, T., and Thoma, M.
TITLE:Simultaneous Fluorometric Determination of Conjugated Fetal Bile Acids in Urine of Newborns by High-Perfomance Liquid Chromatoguraphy.
JOURNAL:Anal. Sci.
VOL:11 PAGE : 91 -96 (1995)
[TOP]

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